Synthesis of Novel Aryl(heteroaryl)sulfonyl Ureas of Possible Biological Interest

The course of reaction of aryl and heteroaryl sulfonamides with diphenylcarbonate (DPC) and 4-dimethylaminopyridine (DMAP) was found to depend on the pKa of the sulfonamide used. Aryl sulfonamides with pK(a) ~ 10 gave 4-dimethylamino-pyridinium arylsulfonyl-carbamoylides, while the more acidic heter...

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Autores principales: Sączewski, Franciszek, Kuchnio, Anna, Samsel, Monika, Łobocka, Marta, Kiedrowska, Agnieszka, Lisewska, Karolina, Sączewski, Jarosław, Gdaniec, Maria, Bednarski, Patrick J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International 2010
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Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6257353/
https://www.ncbi.nlm.nih.gov/pubmed/20335967
http://dx.doi.org/10.3390/molecules15031113
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author Sączewski, Franciszek
Kuchnio, Anna
Samsel, Monika
Łobocka, Marta
Kiedrowska, Agnieszka
Lisewska, Karolina
Sączewski, Jarosław
Gdaniec, Maria
Bednarski, Patrick J.
author_facet Sączewski, Franciszek
Kuchnio, Anna
Samsel, Monika
Łobocka, Marta
Kiedrowska, Agnieszka
Lisewska, Karolina
Sączewski, Jarosław
Gdaniec, Maria
Bednarski, Patrick J.
author_sort Sączewski, Franciszek
collection PubMed
description The course of reaction of aryl and heteroaryl sulfonamides with diphenylcarbonate (DPC) and 4-dimethylaminopyridine (DMAP) was found to depend on the pKa of the sulfonamide used. Aryl sulfonamides with pK(a) ~ 10 gave 4-dimethylamino-pyridinium arylsulfonyl-carbamoylides, while the more acidic heteroaryl sulfonamides (pK(a) ~ 8) furnished 4-dimethylaminopyridinium heteroarylsulfonyl carbamates. Both the carbamoylides and carbamate salts reacted with aliphatic and aromatic amines with the formation of appropriate aryl(heteroaryl)sulfonyl ureas, and therefore, can be regarded as safe and stable substitutes of the hazardous and difficult to handle aryl(heteroaryl)sulfonyl isocyanates.
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spelling pubmed-62573532018-12-04 Synthesis of Novel Aryl(heteroaryl)sulfonyl Ureas of Possible Biological Interest Sączewski, Franciszek Kuchnio, Anna Samsel, Monika Łobocka, Marta Kiedrowska, Agnieszka Lisewska, Karolina Sączewski, Jarosław Gdaniec, Maria Bednarski, Patrick J. Molecules Article The course of reaction of aryl and heteroaryl sulfonamides with diphenylcarbonate (DPC) and 4-dimethylaminopyridine (DMAP) was found to depend on the pKa of the sulfonamide used. Aryl sulfonamides with pK(a) ~ 10 gave 4-dimethylamino-pyridinium arylsulfonyl-carbamoylides, while the more acidic heteroaryl sulfonamides (pK(a) ~ 8) furnished 4-dimethylaminopyridinium heteroarylsulfonyl carbamates. Both the carbamoylides and carbamate salts reacted with aliphatic and aromatic amines with the formation of appropriate aryl(heteroaryl)sulfonyl ureas, and therefore, can be regarded as safe and stable substitutes of the hazardous and difficult to handle aryl(heteroaryl)sulfonyl isocyanates. Molecular Diversity Preservation International 2010-02-26 /pmc/articles/PMC6257353/ /pubmed/20335967 http://dx.doi.org/10.3390/molecules15031113 Text en © 2010 by the authors; http://creativecommons.org/licenses/by/3.0/ licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Sączewski, Franciszek
Kuchnio, Anna
Samsel, Monika
Łobocka, Marta
Kiedrowska, Agnieszka
Lisewska, Karolina
Sączewski, Jarosław
Gdaniec, Maria
Bednarski, Patrick J.
Synthesis of Novel Aryl(heteroaryl)sulfonyl Ureas of Possible Biological Interest
title Synthesis of Novel Aryl(heteroaryl)sulfonyl Ureas of Possible Biological Interest
title_full Synthesis of Novel Aryl(heteroaryl)sulfonyl Ureas of Possible Biological Interest
title_fullStr Synthesis of Novel Aryl(heteroaryl)sulfonyl Ureas of Possible Biological Interest
title_full_unstemmed Synthesis of Novel Aryl(heteroaryl)sulfonyl Ureas of Possible Biological Interest
title_short Synthesis of Novel Aryl(heteroaryl)sulfonyl Ureas of Possible Biological Interest
title_sort synthesis of novel aryl(heteroaryl)sulfonyl ureas of possible biological interest
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6257353/
https://www.ncbi.nlm.nih.gov/pubmed/20335967
http://dx.doi.org/10.3390/molecules15031113
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